204274-29-3

Usage

Uses

Used in Pharmaceutical Synthesis:
(2S)-Methyl 1-(1-phenylethyl)azetidine-2-carboxylate is used as an intermediate or building block in the synthesis of pharmaceuticals and other organic compounds. Its structural features and potential biological activity make it a promising candidate for medicinal chemistry and drug development.
Used in Medicinal Chemistry:
(2S)-Methyl 1-(1-phenylethyl)azetidine-2-carboxylate is used as a versatile compound in medicinal chemistry for its potential to contribute to the development of new drugs. The presence of the azetidine ring and the phenylethyl side chain allows for further investigation in drug discovery and development, potentially leading to innovative treatments and therapies.
Used in Organic Chemistry Research:
(2S)-Methyl 1-(1-phenylethyl)azetidine-2-carboxylate is used as a valuable compound in the field of organic chemistry, where it can be employed in various research projects to explore its properties, reactivity, and potential applications in the synthesis of complex organic molecules.

Upstream product

• 921600-20-6 dimethyl (1'S)-1-(1'-methyl)benzylazetidine-2,2-dicarboxylate 
• 921600-22-8 dimethyl (1'S)-(1'-methyl)benzylaminomalonate 
• 204274-30-6 methyl (2R,1'S)-1-(1'-methyl)benzylazetidine-2-carboxylate 
• 29547-04-4 methyl 2,4-dibromobutanoate 
• 2627-86-3 (S)-1-phenyl-ethylamine 

Downstream Products

• 204274-33-9 (2S,1'S)-1-(1'-methyl)benzylazetidine-2-carboxylic acid 
• 869800-24-8 [1(1S),2S]-1-(1-phenyl-ethyl)-azetidine-2-carbonitrile 
• 1212462-95-7 diphenyl-[1-((1S)-phenylethyl)azetidin-(2S)-yl]methanol 

Relevant academic research and scientific papers

Synthesis of optically active 2-substituted azetidine-2-carbonitriles from chiral 1-arylethylamineviaα-alkylation ofN-borane complexes

The base-promoted α-alkylation ofN-((S)-1-arylethyl)azetidine-2-carbonitriles3viaformation of theirN-borane complexes4was investigated. For example, treatment of diastereomerically pure boraneN-((S)-1′-(4′′-methoxyphenyl)ethyl)azetidine-2-carbonitrile complex (1S,2S,1′S)-4bwith 1.2 equivalents of LDA at ?78 °C followed by 1.3 equivalents of benzyl bromide at ?78 °C and warming to room temperature produced α-benzylated (2S,1′S)-5bain 72% yield and (2R,1′S)-5bain 2% yield. A mechanism for this diastereoselective α-alkylation was proposed. Our method enables the production of optically active 2-substituted azetidine-2-carbonitriles, such as α-benzylated (S)-10aand (R)-10a, starting from commercially available (S)-(1-(4-methoxyphenyl)ethyl)amine.

Enantioselective addition of alkynylzinc to arylaldehydes catalyzed by azetidino amino alcohols bearing an additional stereogenic center

Chiral azetidino amino alcohol ligands bearing an additional stereogenic center were readily prepared and used as catalysts for the asymmetric addition of alkynylzinc to aromatic aldehydes with enantioselectivities of up to 87% ee. The relationship betwee

Efficient route to (S)-azetidine-2-carboxylic acid

A new and efficient route to (S)-azetidine-2-carboxylic acid (>99.9% ee) in five steps and total yield of 48% via malonic ester intermediates was established. As the key step, efficient four-membered ring formation (99%) was achieved from dimethyl (S)-(1′-methyl)benzylaminomalonate by treating with 1,2-dibromoethane (1.5 eq) and cesium carbonate (2 eq) in DMF. Krapcho dealkoxycarbonylation of dimethyl (1′S)-1-(1′-methyl) benzylazetidine-2,2-dicarboxylate, the product of this cyclization procedure, proceeded with preferential formation (2.7:1, 78% total yield) of the desired (2S,1′S)-monoester, with the help of a chiral auxiliary which was introduced on the nitrogen atom. The undesired (2R,1′S)-isomer could be converted to that with proper stereochemistry, by a deprotonation and subsequent reprotonation step. Finally, lipase-catalyzed preferential hydrolysis of the (2S,1′S)-monoester and subsequent deprotection provided enantiomerically pure (S)-azetidine-2-carboxylic acid in a 91% yield from the mixture of (2S,1′S)- and (2R,1′S)-isomers.

Azetidine based ligands in boron catalyzed asymmetric

The preparation of a new class of azetidine-based auxiliaries and their selectivity in the BBr3 catalyzed Diels-Alder reaction is described. The results are compared with a similar proline-derived ligand and a known prolinol auxiliary. Results show that selectivities are highly dependent on the dienophile and the substituent of the chiral auxiliary.

Synthesis and X-ray analysis of 1-((1S)-phenylethyl)-azetidine-(2R)-piperidinamide

The crystal and molecular structure of a new azetidine-2-carboxylic amide derivative is described. The structure was solved by direct methods and refined by least squares methods to R1 = 0.0393 for 4264 reflections (with I > 2σ(I)). The structure consists